LL Cool J
Young LL Cool J with the leather, contrast piping bucket hat. At this point, he's practically the hat's mascot within larger hip-hop culture. As most school photos and portraits tend to go, LL looks caught off guard and completely unpoised. An extra awkward shout-out to his shirt-fastener/brooch/collar bling and the lightly floral velvet shirt he chose to accompany his headgear.